CN106349451B - 用于制备疏水改性环氧烷氨基甲酸酯聚合物的方法 - Google Patents
用于制备疏水改性环氧烷氨基甲酸酯聚合物的方法 Download PDFInfo
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Abstract
本发明涉及一种组合物,其包含疏水改性环氧烷氨基甲酸酯聚合物(HEUR)、铋盐和至少一种减少沉积的化合物的水溶液,所述减少沉积的化合物选自由柠檬酸或其盐、葡萄糖酸或其盐,和乙二胺四乙酸的盐组成的群组。具有特定减少沉积的化合物的所述组合物在该溶液的热老化测试中表现出优异的沉积和颜色形成减少。
Description
技术领域
本发明涉及一种用于制备疏水改性环氧烷氨基甲酸酯聚合物,特别是用铋催化剂制备的疏水改性环氧烷氨基甲酸酯聚合物的方法。
背景技术
疏水改性环氧烷氨基甲酸酯聚合物(hydrophobically modified ethyleneoxide urethane polymer,HEUR)是通常用于增稠涂料配制品的流变改性剂。HEUR通常通过在有机锡催化剂存在下使聚乙二醇、聚异氰酸酯和封端剂一起反应来制备;尽管用于制备该聚合物的锡催化剂的浓度较低,但是环境压力促使行业用环境上更能接受的催化剂(例如铋盐)来替代有机锡催化剂。尽管是环境友好的,但是已知此类催化剂导致成品中的沉淀量或沉积量不期望地高,并且导致不期望的颜色。因此,期望寻求环境上可接受的方式来制备HEUR,并且在热老化期间不会显著形成沉淀物或沉积或者颜色。
发明内容
在一个方面,本发明通过提供包括以下步骤的方法解决了本领域中的需求:使疏水改性环氧烷氨基甲酸酯聚合物与水和至少一种减少沉积的化合物接触以形成溶液,所述减少沉积的化合物是柠檬酸或其盐、葡萄糖酸或其盐,或者乙二胺四乙酸的盐;其中所述疏水改性环氧烷氨基甲酸酯聚合物包含5至1000ppm的铋盐,其中所述减少沉积的化合物的浓度为基于所述溶液之重量的0.05至4重量百分比,并且所述疏水改性环氧烷氨基甲酸酯聚合物的浓度为基于所述溶液之重量的12至50重量百分比。
在另一个方面,本发明是一种组合物,其包含疏水改性环氧烷氨基甲酸酯聚合物、铋盐和至少一种减少沉积的化合物的水溶液,所述减少沉积的化合物是柠檬酸或其盐、葡萄糖酸或其盐,或者乙二胺四乙酸的盐(EDTA盐),其中所述疏水改性环氧烷氨基甲酸酯聚合物的浓度12至50重量百分比,所述铋盐的浓度为5至1000ppm,并且所述减少沉积的化合物的浓度为0.05至4重量百分比,全部基于所述溶液的重量。
具体实施方式
在第一方面,本发明是一种包括以下步骤的方法:使疏水改性环氧烷氨基甲酸酯聚合物与水和至少一种减少沉积的化合物接触以形成溶液,所述减少沉积的化合物是柠檬酸或其盐、葡萄糖酸或其盐,或者乙二胺四乙酸的盐;其中所述疏水改性环氧烷氨基甲酸酯聚合物包含5至1000ppm的铋盐,其中所述减少沉积的化合物的浓度为基于所述溶液之重量的0.05至4重量百分比,并且所述疏水改性环氧烷氨基甲酸酯聚合物的浓度为基于所述溶液之重量的12至50重量百分比。
本文中使用的“疏水改性环氧烷氨基甲酸酯聚合物”指疏水改性环氧乙烷氨基甲酸酯聚合物(hydrophobically modified ethylene oxide urethane polymer,HEUR)、疏水改性环氧丙烷氨基甲酸酯聚合物、疏水改性环氧乙烷/环氧丙烷氨基甲酸酯共聚物、疏水改性环氧乙烷/环氧丁烷氨基甲酸酯共聚物或疏水改性环氧乙烷/环氧丙烷/环氧丁烷氨基甲酸酯三聚物。优选地,所述疏水改性环氧烷氨基甲酸酯聚合物是疏水改性环氧乙烷氨基甲酸酯聚合物(HEUR)。疏水改性环氧烷氨基甲酸酯聚合物可以以多种方式制备,例如US2009/0318595 A1、US 4,155,892、US 7,741,402和美国专利公开2013/0158194中公开的那些方法。
用于本发明方法的疏水改性环氧烷氨基甲酸酯聚合物在例如以下铋盐存在下制备而成:醋酸铋、2-乙基己酸铋、正己酸铋、正辛酸铋、新癸酸铋和环烷酸铋。将含铋的疏水改性环氧烷氨基甲酸酯聚合物与减少沉积的化合物和水组合并任选地与其它添加剂组合以形成含铋疏水改性环氧烷氨基甲酸酯聚合物的溶液。基于所述溶液的重量,减少沉积的化合物的浓度为优选从0.1重量百分比,更优选从0.2重量百分比至3重量百分比,更优选至2重量百分比,并且最优选至1重量百分比。基于所述溶液的重量,疏水改性环氧烷氨基甲酸酯聚合物的浓度为优选从15重量百分比至优选40重量百分比,更优选25重量百分比;基于所述溶液的重量,铋盐的浓度为优选从10ppm,更优选从20ppm至优选500ppm,更优选至200ppm,并且最优选至100ppm。对于含有柠檬酸和葡萄糖酸或其盐或者其组合的溶液,pH优选在2.5至6,更优选至5的范围内。对于含有EDTA盐的溶液,pH优选在从7.5,更优选从8至11,更优选至10的范围内。所述溶液还可含有其它降低溶液黏度的添加剂(例如寡糖,例如环糊精)以及杀生物剂和pH调节剂。
已令人吃惊地发现,在热老化测试中表现出可接受低的沉积和颜色形成的仅有化合物是柠檬酸、葡萄糖酸,和乙二胺四乙酸的盐。柠檬酸经证明在减少沉积和颜色方面格外有效。
实例
中间体实例1-Bi催化性HEUR的制备
将CARBOWAXTM聚乙二醇8000(200.0g,陶氏化学公司(The Dow Chemical Company)或其附属公司的商标)和甲苯(325.0g)的混合物通过共沸蒸馏干燥,然后在反应容器中于N2下冷却至90℃。在持续1小时的搅拌下,向该容器添加4,4'-亚甲基双(异氰酸环己酯)(8.8g)和2-乙基己酸铋(28%Bi,0.2g),在此之后添加正癸醇(3.4g)。在90℃下继续再搅拌1小时,随之在甲苯蒸发之后分离所得固体聚合物。通过使用聚环氧乙烷标准物的尺寸排阻色谱(by size exclusion chromatography,SEC),Mw为40,000道尔顿。
候选物的筛选
进行一系列实验以寻求用于减少沉积和颜色的合适候选物(酸,大部分情况下)。在2.1至6.5的pH下,使用含2-乙基己酸铋(700ppm)的水/丁基卡必醇(50:50w/w)与多种酸的组合来制备溶液。将丁基卡必醇和水的混合物(18g)置于玻璃瓶中,之后添加酸、寡糖和缓冲液添加剂至目标pH。摇动瓶子,然后添加2-己基己酸铋。在3天的热老化之后,在60℃下测量pH并测量沉积和颜色。表1概括了受试材料的沉积和颜色形成。对沉积和颜色使用0至3的评级。对于两者,认为0或1的评级是可接受的。
对于沉积,
0=没有形成沉积的迹象;
1=痕量的沉积形成;
2=在瓶底部具有超过痕量但<1mm的沉积形成;和
3=>1mm沉积形成。
对于颜色,
0=没有颜色的迹象;
1=些许颜色(通常为红色或褐色);
2=明显的红色或褐色;
3=强着色。
表1-沉积和颜色筛选结果
筛选显示,仅3种候选物适于沉积和颜色减少:柠檬酸、葡萄糖酸和EDTA。如下一部分中所述制备Bi催化性中间体1HEUR与这些材料中每一种的水溶液。
实例1-制备Bi催化性HEUR与柠檬酸的低pH溶液
在室温下,将杀生物剂(14ppm)、柠檬酸(0.25g)、寡糖(4.2g,50%活性物)和中间体实例1(8.75g)溶解于水(36.3g)中过夜。用NaOH将该溶液的pH调节至4.1。
实例2-制备Bi催化性HEUR与葡糖酸的低pH溶液
该实例基本上如实例1中所述制备,不同之处在于使用葡萄糖酸(0.5g,50%水溶液)代替柠檬酸。pH为2.9。
实例3-制备Bi催化性HEUR与EDTA的高pH溶液
该实例基本上如实例1中所述制备,不同之处在于使用EDTA(0.0.25g)代替柠檬酸。用10%NaOH将该溶液的pH调节至9.3。
比较例1-在无减少沉积的化合物下制备Bi催化性HEUR的溶液
该实例基本上如实例1中所述制备,不同之处在于未添加减少沉积的化合物。该样品的pH为7.2。
比较例2-制备Bi催化性HEUR与EDTA的低pH溶液
该实例基本上如实例3中所述制备,不同之处在于该溶液的pH为3.9。
在于60℃下热老化3天之后,评价实例1-3以及比较例1和2的沉积和颜色。减少沉积的化合物(sediment abating compound,SAC)对沉积形成和颜色的影响示于表1中。
表1-HEUR和添加剂对沉积和颜色形成的影响
实例 | SAC | % | pH | 沉积 | 颜色 |
实例1 | 柠檬酸 | 0.5 | 4.1 | 0 | 0 |
实例2 | 葡萄糖酸 | 0.5 | 2.9 | 1 | 0 |
实例3 | Na EDTA | 0.5 | 9.3 | 0 | 1 |
比较例1 | 对照 | 0 | 7.2 | 2 | 2 |
比较例2 | EDTA | 0.5 | 3.9 | 2 | 1 |
表1显示含有柠檬酸、葡萄糖酸或EDTA钠盐的Bi催化性HEUR均通过沉积和颜色测试。尽管发现EDTA在水和丁基卡必醇中在pH 3.9下在初始筛选测试中是可接受的,但是发现其在纯粹水中表现出较高的沉积形成,推测这是由于其水溶解度较低。然而,在pH为9.3时,Na EDTA获得优异结果。
Claims (10)
1.一种包括以下步骤的方法:使疏水改性环氧烷氨基甲酸酯聚合物与水和至少一种减少沉积的化合物接触以形成溶液,所述减少沉积的化合物是柠檬酸或其盐、葡萄糖酸或其盐,或者乙二胺四乙酸的盐;其中所述疏水改性环氧烷氨基甲酸酯聚合物包含5至1000ppm的铋盐,其中所述减少沉积的化合物的浓度为基于所述溶液之重量的0.05至4重量百分比,并且所述疏水改性环氧烷氨基甲酸酯聚合物的浓度为基于所述溶液之重量的12至50重量百分比。
2.如权利要求1所述的方法,其中所述疏水改性环氧烷氨基甲酸酯聚合物的浓度为基于所述溶液之重量的15至40重量百分比;并且所述铋盐的浓度为基于所述溶液之重量的10至200ppm。
3.如权利要求2所述的方法,其中所述减少沉积的化合物的浓度为基于所述溶液之重量的0.1至3重量百分比,所述溶液的pH在2.5至6的范围内,并且所述减少沉积的化合物是柠檬酸或其盐或者其组合。
4.如权利要求2所述的方法,其中所述减少沉积的酸的浓度为基于所述溶液之重量的0.1至3重量百分比,所述溶液的pH在2.5至6范围内,并且所述减少沉积的化合物是葡萄糖酸或其盐或者其组合。
5.如权利要求2所述的方法,其中所述减少沉积的酸的浓度为基于所述溶液之重量的0.1至3重量百分比,所述溶液的pH在7.5至11的范围内,并且所述减少沉积的化合物是乙二胺四乙酸的盐。
6.一种组合物,其包含疏水改性环氧烷氨基甲酸酯聚合物、铋盐和至少一种减少沉积的化合物的水溶液,所述减少沉积的化合物是柠檬酸或其盐、葡萄糖酸或其盐,或者乙二胺四乙酸的盐,其中所述疏水改性环氧烷氨基甲酸酯聚合物的浓度是12至50重量百分比,所述铋盐的浓度为5至1000ppm,并且所述减少沉积的化合物的浓度为0.05至4重量百分比,全部基于所述溶液的重量。
7.如权利要求6所述的组合物,其中所述疏水改性环氧烷氨基甲酸酯聚合物的浓度为基于所述溶液之重量的15至40重量百分比;并且所述铋盐的浓度为基于所述溶液之重量的10至200ppm。
8.如权利要求7所述的组合物,其中所述减少沉积的化合物的浓度为基于所述溶液之重量的0.1至3重量百分比,所述溶液的pH在2.5至6的范围内,并且所述减少沉积的化合物是柠檬酸或其盐或者其组合。
9.如权利要求7所述的组合物,其中所述减少沉积的化合物的浓度为基于所述溶液之重量的0.1至3重量百分比,所述溶液的pH在2.5至6的范围内,并且所述减少沉积的化合物是葡糖酸或其盐或者其组合。
10.如权利要求7所述的组合物,其中所述减少沉积的化合物的浓度为基于所述溶液之重量的0.1至3重量百分比,所述溶液的pH在7.5至11的范围内,并且所述减少沉积的化合物是乙二胺四乙酸的盐。
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MY197262A (en) | 2015-07-27 | 2023-06-08 | Chong Kun Dang Pharmaceutical Corp | 1,3,4-oxadiazole sulfonamide derivative compounds as histone deacetylase 6 inhibitor, and the pharmaceutical composition comprising the same |
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CN107737536A (zh) * | 2017-09-30 | 2018-02-27 | 浙江海洋大学 | 一种铋盐的溶解方法 |
KR102316234B1 (ko) | 2018-07-26 | 2021-10-22 | 주식회사 종근당 | 히스톤 탈아세틸화효소 6 억제제로서의 1,3,4-옥사다이아졸 유도체 화합물 및 이를 포함하는 약제학적 조성물 |
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US10150852B2 (en) | 2018-12-11 |
BR102016015624A2 (pt) | 2017-07-25 |
US20190040229A1 (en) | 2019-02-07 |
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